Anisole → 1'H-1,3'-Bipyrrol-2'-yl(2-methoxyphenyl)methanone

HRID 523878노트

반응식

HRID 523878 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Li]CCCC.CCCCCC.C1(OC)C=CC=CC=1.[N:29]1([C:34]2[CH:38]=[CH:37][NH:36][C:35]=2[C:39](OCC)=[O:40])[CH:33]=[CH:32][CH:31]=[CH:30]1.[NH4+].[Cl-]>C1COCC1>[N:29]1([C:34]2[CH:38]=[CH:37][NH:36][C:35]=2[C:39]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])=[O:40])[CH:30]=[CH:31][CH:32]=[CH:33]1

참가 물질

8

반응물 6

HCID 7519Anisole2회HCID 8058HexaneHCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 53253731ethyl 1'H-[1,3'-bipyrrole]-2'-carboxylate2회HCID 178418339Butyllithium

생성물 1

HCID 532537321'H-1,3'-Bipyrrol-2'-yl(2-methoxyphenyl)methanone수율 85.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-bromoanisole (1.39 g, 7.43 mmol, 5.63 equiv) in anhydrous THF (5 mL) at −78° C., a 2.5M solution of BuLi in hexane (3 mL, 7.50 mmol, 5.68 eq.) was added dropwise, the resulting mixture was stirred for 1 h. at −78° C. to generate the lithiated anisole. In an oven-dried flask, compound (c) (270 mg, 1.32 mmol, 1 eq.) was dissolved in THF (5 mL) and cooled to −78° C., the lithiated anisole (d) was transferred into the solution containing (c) dropwise via syringe, and the resulting mixture was stirred for 1 h. at −78° C. To the reaction mixture, an aqueous solution of NH4Cl (5 mL) was added, the mixture was extracted with EtOAc, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography (10% EtOAc in Hexane) to give (e) as a light brown solid (0.30 g, 85% yield).

후처리

  1. temperaturecooled to −78° C.
  2. stirringthe resulting mixture was stirred for 1 h. at −78° C
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe crude product was purified by flash column chromatography (10% EtOAc in Hexane)

출처 및 근거

ORD 기록
ord-3af0018848634a89881b04f280f78365
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340501B2

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